LIPIDS

Structure, Classification and

Nomenclature

Don M. Abrina, M.D.

 Lipids
 Heterogenous group of compounds
related more by their physical rather
than their chemical properties
 Common properties:
1) Insoluble in water
2) Soluble in non-polar solvents
3) Found in animal and plant tissues
 Types of lipids
1) Fats

2) Oils

3) Steroids

4) waxes
 Functions
1) Efficient source of energy in the body
2) Serves as thermal insulator in
subcutaneous tissue
3) Electrical insulators
4) Important cellular constituents
 Classification
1) Simple lipids-esters of fatty acids with
alcohols
a) Fats-esters of fatty acid with glycerol
b) Waxes-esters of fatty acid with higher
molecular weight monohydric alcohols
 Classification….
2) Complex lipids-esters of fatty acid
containing groups in additon to an
alcohol and a fatty acid
a) Phospholipids-lipids containing a
phosphoric acid residue aside from a
fatty acid and alcohol
Phospholipid
 Classification…..
b) Glycolipids- lipids containing
sphingosine and carbohydrate
c) Others: sulfolipids, aminolipids,
lipoproteins
 Classification….
3) Precursor and derived lipids- fatty
acids, glycerol, steroids, lipid-soluble
vitamins and hormones
4) Neutral lipids- uncharged lipids
including acylglycerols, cholesterol
and cholesteryl esters
 Fatty Acids
 Long- chain hydrocarbon molecules
 Exist as free fatty acids (unesterified)
and fatty acyl esters
 Two major roles in the body:
1. As the components of more complex
membrane lipids
2. As the major components in stored fat
 plasma free fatty acids- transported by
serum albumin
 fatty acids- oxidized by the liver and
muscle to provide energy
 also precursors of many compounds such
as glycolipids, phospholipids, sphingolipids
and prostaglandins
 Triacyglycerols- major energy reserve of
the body
Triglyceride
 CH3(CH2)nCOO-
 chemical formula of a fatty acid
 made up of a hydrocarbon chain with a
terminal carboxyl group
 terminal carboxyl group has an affinity
for water making fatty acids amphipathic
in nature
 long-chain fatty acids- predominantly
hydrophobic region
 Classification of fatty acids

1. Saturated fatty acids- fatty acid chains

which contain no carbon-carbon
double bonds
- palmitic acid (16:0)
- Resistant to oxidation outside the body
Palmitic acid (16:0)
Saturated fatty acid
 Classification of fatty acids….

2. Unsaturated fatty acids- contain one or

more carbon-carbon double bonds
- oleic acid [18:1(9)]
- Oxidized in the presence of air
(rancidification)
Unsaturated fatty acids
Saturated and unsaturated
 Nomenclature of Fatty Acids
 the carbon atoms- numbered beginning
with the carboxyl carbon as carbon 1
 E.g. arachidonic acid (20:4) (5,8,11,14)
 20 carbons long
 4 double bonds
 Between carbons 5-6, 8-9, 11-12, 14-15
Arachidonic acid
 Nomenclature….
 the carbon to which the carboxyl group
is attached (c2) is called the  carbon
 carbons 3 and 4 are the  and  carbon
 the terminal methyl carbon is the 
carbon or the n-carbon atom
Greek letter designation
 Nomenclature….
 when double bonds are present, they
are nearly always in the cis rather than
the trans configuration
Cis and trans configuration
 Nomenclature….
 The introduction of a cis double bond
causes the fatty acid to “kink”
 If the fatty acid has two or more double
bonds- they are always spaced at 3
carbon intervals
Kinking of fatty acid
 Three carbon intervals

Linolenic polyunsaturated fatty acid

 unsaturated fatty acids:
1. Monounsaturated fatty acids
E.g. oleic acid (18:1; 9)- most common
fatty acid in natural fats
2. Polyunsaturated fatty acids
E.g. arachidonic acid (20: 4; 5,8,11,14)-
precursor of prostaglandins
 Oleic acid

 monounsaturated -9 fatty acid

 Arachidonic acid

 polyunsaturated fatty acid

3. Specialized fatty acids- prostaglandins,
thromboxanes and leukotrienes
- collectively known as eicosanoids
- Derived from -eicosa (20 carbon) fatty
acid
- Dietary precursor is the essential fatty
acid linoleic acid
 Essential fatty acids
1) Linoleic acid- (18:2; 9,12)
-  -6 fatty acid ( the closest double
bond to the -end begins 6 carbons
from the end )
2) Linolenic acid- (18:3; 9,12,15)
- -3 fatty acid
 Linoleic acid

 -6 fatty acid

 Linolenic acid

 -3 fatty acid

 Phospholipids
 main lipid constituent of cell
membranes
 polar ionic compounds composed of an
alcohol attached to a diacylglycerol or
sphingosine
 amphipathic in nature- hydrophilic head
and a long hydrophobic tail
 Classes of phospholipids
1. Those that have glycerol as a backbone
- called phosphoglycerides
- Major class of phospholipids
- Found as membrane components
- Essential components of bile
- Anchors for some proteins to cell
membranes
- Participates in signal transmission across
membranes
- Components of lung surfactant
 phosphoglycerides- contain
phosphatidic acid (diacylglycerol with a
phosphate group on the third carbon)
 phosphatidic acid- simplest
phosphoglyceride and is the precursor of
other members:
1. Phosphatidylcholine- lecithin
- choline + phosphatidic acid
2. Phosphatidylethanolamine- cephalin
- ethanolamine + phosphatidic acid
3. Phosphatidylinositol- inositol + phosphatidic
acid
4. Phosphatidylserine- serine + phosphatidic
acid
5. Phosphatidylglycerol- glycerol + phosphatidic
acid
6. Plasmalogens- constitute 10% of the
phospholipids of brain and muscle
- fatty acid attached by an ether rather than an
ester linkage at carbon 1 of the core glycerol
molecule
- Phosphatidalethanolamine is the
plasmalogen of phosphatidylethanolamine
 Phosphoglyceride Plasmalogen

 ether linkage
 Classes of phospholipids…..

2. Those that have sphingosine instead of

glycerol as a backbone
- a fatty acid is attached to the amino group
of sphingosine
- This produces a ceramide
- The alcohol group of carbon 1 is esterified
into phosphorylcholine producing
sphingomyelin
Sphingosine
Ceramide
 Glycolipids
 also known as glycosphingolipids
 contain ceramide (fatty acid +
sphingosine) + one or more sugars
 located in outer layer of plasma
membrane
 source of ABO blood group antigens
 cell surface receptors for toxins and
viruses
 Glycolipids differ from sphingomyelin:
1) Contains no phosphate
2) Polar head function - provided by a
monosaccharide or an oligosaccharide
attached to ceramide by an O-
glycosidic bond
Glycosphingolipid
 Classes of glycosphingolipids:

A. Neutral glycosphingolipids
1. Cerebrosides - simplest neutral
glycosphingolipid
- ceramide monosaccharide that may
contain galactose (galactocerebroside)
or glucose (glucocerebroside)
- High concentration in myelin sheath
B. Acidic glycosphingolipids
1. Gangliosides - most complex
- found in ganglion cells of the CNS
- Accumulation leads to Tay Sach’s Disease
2. Sulfatides - cerebrosides that contain
galactosyl residues that is sulfated at c3 of
the galactose
- globoside
- Accumulation leads to Fabry’s Disease
 Steroids
 derivatives of
cyclopentanoperhydrophenanthrene
 the steroid nucleus - rigid planar
structure resembling phenanthrene
 cholesterol - best known steroid
Steroid carbon skeleton
A. Sterols - steroids with 8-10 carbon
atoms in the side chain at c17 and an
alcohol hydroxyl group at c3.
e.g: cholesterol
B. Cholesteryl ester - a fatty acid is
attached to c3 instead of an -OH
- very hydrophobic
- Must be transported via lipoproteins or
solubilized by bile salts in the bile
 cholesterol - side chain at c17 and an
alcohol hydroxyl group at c3
 Cholesterol

Precursor of other steroids:

1. Bile acids
2. Adrenocortical hormones
3. Sex hormones
4. D vitamins
 Eicosanoids
 class of lipids that include
prostaglandins, thromboxanes and
leukotrienes
 functions like hormones except that
they act locally and catabolized rapidly
Structure of prostaglandins
Leukotrienes
Prostaglandins and thromboxanes